Frat Boy Turned - Virgin No More

The next couple of days were pretty uneventful. At least in terms of fun with Connor. He had a big exam that week, so he was pretty preoccupied studying all week. He didn't pay much attention to me at all other than the occasional cage check. Meanwhile, I was going crazy. I couldn't focus on anything school related due to my insane level of horniness.

Jess and Connor made it clear that I wasn't going to be unlocked anytime soon, so I kind of accepted that. I knew not to question them. But that didn't stop me from playing with myself, it just looked a little different than it did before. Jess let me stay at her house whenever I wanted, so I was over there quite a bit. I had everything an eager sissy needed -- a huge girly room, tons of panties and girly outfits, a huge tv for whatever hypno I wanted to watch, and soooo many toys to try.

So while Connor was busy studying for class, I was busy studying how to be a better sissy girl. While I loved the vibrating plug Jess had showed me before, I quickly wanted more. Plus all of the hypno I was watching focused on real cocks, so the best I could do was to use some of the dildos that Jess had.

I got back from class one day to find Jess had gone to work. She left a note on the fridge that read "Riley, I'm working late tonight. There's a protein shake for you in the fridge. I left some new toys for you in your room. <3"

New toys?! I could already feel the precum leaking into my panties. I scurried to my room to find a 9" dildo attached to a fucking machine next to my dresser. There was an identical dildo and machine about two feet in front of the first one. I was a bit overwhelmed, as I definitely hadn't taken anything that big in my boi pussy yet. But I giggled with excitement as I realized it was about the same size as Connor's cock. I squatted in front of the dildo and quickly put it in my mouth. I immediately could tell it was a little thinner than Connor's - thankfully. I don't think my boi pussy could stretch enough to fit his yet.

I started to pull my clothes off and then found another note on the bed next to a little box.

"I talked with Connor. He's super busy with schoolwork, but doesn't want your training to fall behind. This is a prototype we just got into the shop - we think you're the perfect one to try it out."

I opened the box to find what looked like a VR headset. I hit the button on the side and both of the fucking machines started slowly thrusting.

"Holy shit, this is all connected." I thought. Before I could think much more, I slipped out of my panties and grabbed some lube. I lubed my hole and the dildo and then positioned myself between the two of them. I lined the dildo up with my pink boi pussy and then pulled the headset over my face.

In that moment, it almost felt like I lost control of my body. I was completely immersed into the headset. I looked around and could see a number muscular guys with huge cocks standing around me. I could even feel what felt like hands grab my waste as I was pulled back onto the dildo. I felt the head of the cock enter my boi pussy and then immediately heard Connor's voice say "Good girl."

How did this feel so real?! I looked in front of me and could see the hard cock right in front of my lips. I opened my mouth and let the cock in and heard him again. "Such a good little sissy girl."

This was crazy. Both of the cocks started thrusting in and out of me, thankfully pretty slowly to start. All I could see through the headset was the cocks and then hypno. There was nowhere to look to escape it. All encouraging me to become a real sissy girl. To never unlock my cock. To exist only to serve real men. To sissygasm. It was so intense.

I don't know how long this went on, but I started to feel a gradual, overwhelming warm sensation within me. This must be a sissygasm I thought. I started getting so excited at the thought of finally cumming, but every time I felt like I was nearing a climax, the cocks would slow down. This went on at least ten times as I would near the edge and then they'd slow down to make sure I couldn't get any relief.

I have no idea how long it lasted, but suddenly I felt the headset flip back over my head and I saw Jess standing over me.

"Based on the puddle and stream of precum coming from your cage, I'm going to say the new toys are a hit??" She said with a giggle.

I couldn't even get words out to answer her. I was too gooned out. All I could think about was how much I needed to hear Connor tell me I was a good girl again.

Jess pulled the dildo out of my boi pussy and I immediately felt empty. She pulled me up off the ground and sat me on the bed. I still couldn't form any words.

"Maybe this was too much. They said it could be very overstimulating." She brought me some water and I gradually came back to reality.

"Omg, that was amazing." I finally said. "I thought I was finally going to cum in my cage, but it kept slowing down right when I got close."

"That's the point, Riley. Connor wants your first sissygasm to come from his cock and his cock only. He wanted it programmed to slow you down anytime you got too close to the edge."

Fuck, I needed to cum so bad. "Can I please play with one of my other dildos, Jess?"

"I think you've had enough fun for today, babe," she replied.

"But pleeeeeeasse, I need it, mistress."

Wait, why did I just call her that? She gave me a hug and then grabbed my hand. "Let's get ready for bed baby. It's late."

I finally looked over at the clock and saw it was 11 PM. I had been in that headset for over 5 hours. "I think you'll need to sleep with me again tonight. I don't think I can trust you on your own when you're this gooned out."

We walked into her bedroom and she opened her panty drawer to grab me a pair. She handed me a baby blue, ribbed Victorias Secret thong. "I can't have you leaking in my sheets all night," she said with another chuckle.

She then handed me a matching babydoll that I pulled on as well. We climbed into bed and I was left to try to calm my mind down enough to sleep. I finally fell asleep about an hour later.

The rest of my week was less eventful. Jess and I played pretty often, but that mainly just consisted of me eating her out. She'd let me put my prostate vibrator in while we played, but I never got enough stimulation to cum of course. Connor finally had his big exam that Friday morning. I couldn't wait to have his attention back.

We had another party planned that Friday night. This one was playboy themed though, so it was strictly the fraternity brothers and their dates. Couldn't risk having just anyone come and possibly get blasted for being misogynistic. That's an easy formula to get cancelled these days. The girls would dress as playboy bunnies, of course. The guys wore either a nice suit or a robe & their boxers -- just depending on how confident they were with their dates.

I knew Connor would be in a robe and I couldn't wait. I was planning on going the suit route, since I definitely didn't have anything to show off under my boxers. That'd be way too risky. That is until Jess told me her plans that morning.

"Remember how I said you should go as Riley to the next party?" she asked.

Immediately, I felt a jolt of nerves come over me. This party was definitely not the one to try that for, I thought.

"Connor wants us both to be his dates to the party tonight. We'll just tell everyone that Ryan went home for the weekend. Riley, however, will get to make her real debut. Connor and I have already discussed it all."

She could see the fear in my eyes, but assured me I didn't have to go if I didn't want to. "Just trust me. I'll doll you up where no one would ever think you were actually a guy."

I still wasn't convinced, but agreed to let her try. I could always back out last minute if I needed to.

"We have all day to get ready, but I think we should start now! It'll be such a fun day."

I guess that meant I wasn't going to class, but not like I'd be able to focus anyway if I did. We went to her bathroom and she ran a bath. She slid out of her little gown, so I followed suit -- feeling my cock twitch in its cage at the sight of her naked body. I don't think she'd ever not turn me on.

"You're so cute, babe. We're going to have so much fun tonight."

We slid into the bath, both shaved our legs, and then soaked for a while, the jacuzzi jets ever so slightly hitting my cage constantly reminding me of my little locked clit.

The water started to get a little cold, so we finally got out and dried off. She grabbed a plug that looked pretty similar to the one I wore to the last party -- this one was a little bigger though. I slid it in and felt the pressure on my prostate. I took the panties that she'd laid out for me and pulled them on. Nothing fancy, just a comfy pair to get ready in. She also had an oversized t shirt for me that I put on as well.

She sat me down at her makeup vanity and spun me around to get to work. I felt the subtle vibrations of the plug start, too. I tried to sit still, so I wouldn't mess up any of her work. She did my makeup for at least an hour it seemed -- even shading my neck too to hide my adam's apple.

"Connor said he wanted us both to curl our hair tonight, so I think this wig will be perfect for you." She fit it over my head and then spun me back to face the mirrors.

She really outdid herself. I really looked like a real girl. My makeup was perfect - not too slutty, just girly. The brown curly hair fell just over my shoulders.

"Go make us some breakfast while I do my makeup, baby."

"Yes, mistress," I replied.

Gosh, there was that word again.

"I love that you're calling me mistress now, Riley. Makes me feel so dominant, and honestly gets me a little wet too."

At least she liked it, I thought. It just felt natural at this point.

I got to work on some breakfast and felt her increase the pulsations of my plug. My knees bucked a little, but I got used to it pretty quick. I knew it still wasn't even at half way based on how intense it had been the weekend before. Every now and then I'd catch a glimpse of my reflection in one of the windows -- it still shocked me every time that I didn't see myself at all. I just saw a really hot girl instead.

After a while, she joined me in the kitchen for breakfast -- really brunch at this point. We sat and ate and she filled me in more on our plans for the rest of the day.

"I have a few options for you to try on for tonight. We can have a little fashion show! You can choose whichever outfit you feel sexiest in. Connor should be here around 6 for dinner and a few drinks - then we'll head to the party after that."

I was so excited to see Connor again. Ever since my fun with the VR headset, all I really wanted was to hear him telling me I was a good girl again.

We went back to Jess's room after we cleaned up and walked into her massive closet. It wasn't hard to see which outfits she had in mind for us. There were three sets of matching outfits - just differing in color.

The first one was the typical bunny outfit. A tiny thong, fishnets, bunny ears, stilettos, and of course the bunny suit -- tight leotard with the puffy bunny tail on the butt.

The second was a little more subtle. Beautiful lingerie, a tight white tank top that stopped above your belly button, booty shorts with the bunny logo covering them, and matching sneakers. And of course, bunny ears. It kind of had a slumber party feel.

The third reminded me of Lola Bunny from Space Jam. Cute lingerie of course, super short basketball shorts that had a bunny tail on them, a matching crop top, tall socks that came up over your knees, and ears to match. I assumed we'd wear the same sneakers from the second option with these.

"Well, what are you waiting for?!" I heard Jess ask. "Which one do you want to try on first?"

I couldn't deny that I was drawn to the classic look. So we went for that one first. I'd never worn fishnets and really wanted to feel how they felt on my smooth legs. I'd never worn heels either, so that'd be exciting. Jess hopped onto the bed to wait for me to get dressed.

I slid the fishnets on first, then slid the thong and bunny suit on over them. I put the heels on next and immediately felt myself wobble. These things were intense!

Jess could hear the stilettos and told me to come show her. So I opened the door and hobbled out, trying to keep my balance. I looked so slutty, but the bunny suit was so tight that you could clearly see the outline of my cage. And without knowing how to walk in heels, we decided this wouldn't work.

I changed into the second outfit. This one was much easier to get on, that's for sure. And I could actually walk! I came to show Jess and she loved it as well. She even pulled out some silicone boobs and a training bra that made the tank top pop even more. My butt looked amazing already, and now my chest did too. I really was completely unrecognizable.

The third outfit was great, too. I really liked the way the long socks felt on my legs. The crop top was a little flowy, but the training bra helped out.

"I don't think I can pick!!" I said. "Could we let Connor choose which one he likes more?"

"Sheesh, you really are his little slut aren't you? Of course we can let him pick. We'll have plenty of time once he gets here. But first, I need your mouth."

She opened her legs and I instinctively went straight for her clit. She turned my plug up even more as I I did, which really drove me crazy. I could feel the wet spot forming in my panties already. Gosh, I loved being controlled by her. I brought her to orgasm as she pushed my head down with her fingers in my long, curly hair.

"I can't wait for you to cum like a girl, baby. You're going to loooove it."

I could only let out a muffled moan as my tongue was still busy pleasing her. As her orgasm faded, she let go of my hair and I came up for air. She pulled me in for a kiss and made out with me before reaching for my cage.

"Your balls are so full. You're going to make such a mess when you finally cum."

"I really hope Connor lets me cum, mistress. I want to cum while he fucks me so bad. I need to be his good girl."

Jess laughed, "I can't believe how fast that trigger took in your brain. Connor said he wanted to embed that in your little sissy mind so you'd long to hear him say those words. I told him it'd take at least a few weeks, but it seems to have worked already. He's going to love that."

I realized just how easily they'd been able to change me over the last few weeks. I was actually going to go to this party as a girl when just two weeks ago I was still trying to fuck girls. Now all I could think about was how good it would feel to have him fuck me. I felt ashamed at how quickly I'd been turned, but that didn't last long as Jess switched up the vibrations of my plug. It started pulsing very hard as I heard another girly moan escape my lips.

"Eh eh eh, don't start changing your mind now Riley. You know you wanted all of this." Jess said.

She was right. As embarrassing as it was, I felt so much happier since they'd taken my keys away than I did before. Maybe I did really want this all along.

I couldn't think about it for too long as she chimed in that we needed to go get dinner ready. Connor would be here in 30 minutes!

I could feel the excitement building as the time ticked on -- and as my plug pulsed against my prostate.

"Go ahead and make some drinks! You know what he likes -- make us two cosmos while you're at it," Jess said.

I was finishing our drinks right as I heard the door open. I grabbed his whiskey and hopped over to the living room.

"Oh, fuck. Jess you outdid yourself again. Riley, you look so sexy. I love the outfit, my little Lola Bunny for the night!"

I was so glad he liked it. I felt my little bunny tail wiggle as I spun around for him.

"I'm going to be the star of the evening with you two sexy girls as my dates. Going to have to keep all the other guys at bay once they see you two," Connor gloated.

Jess explained how I wanted to show him both outfits to choose from, so I ran back to the bedroom to change back to the slumber party option. But Connor really liked the sporty look, so he told me to keep it on. Jess went back to put her matching outfit on as Connor and I finished our drinks.

We ate dinner, had a few more drinks and finally it was time to leave. Jess and I went to freshen up. I looked at myself in the mirror again, surprisingly confident that I looked nothing like Ryan. I couldn't believe I was actually going to do this.

"Connor wants you to size up, babe," said Jess as she handed me an even bigger plug.

Gosh, it was big. But I knew I had to. I lubed it up and went to swap them. It was so big. I felt my hole stretch as I pushed it in and finally it snatched into place. I pulled my panties and shorts back on and slipped into my sneakers. Jess gave me one last kiss as we walked back out to leave.

Connor gave us both a tequila shot, which I welcomed. Then we headed to the party. He grabbed my ass on the way to the car as he commented on my walk.

"Looks like that plug really is a little big for you. I love how it makes your hips swing as you walk, sissy."

I blushed as I slid into the car seat.

He switched the pulsing on during the ride and I knew I was in for a long night. Precum was already flowing from my cage.

We arrived at the frat house and the debauchery had already started. Drinks were flowing, music was bumping, there were tons of scantily clad girls grinding all over the guys. Yet when we walked it, it felt like everyone noticed.

I felt my face glowing red. I really was doing this. Connor grabbed us some drinks from our room and we joined in. Jess and I taking turns grinding on Connor. I loved feeling his cock grow and twitch against my ass as he grabbed and groped me.

Thankfully he protected me from dancing with any of the other guys for too long. They'd come and grab me every now and then and I'd tease them a bit, but never long enough for them to really start feeling around on me too much before Connor would slip back in. I couldn't believe that I was grinding on my pledge brothers. And that they all thought I was a real girl. I'd hear them comment to Connor when he slid back behind me about how tight my ass was or how perky my tits were. Some of the bolder ones would even whisper about how tight my pussy was -- probably would bother a normal girl, but I loved hearing all of the dirty talk.

It was such a rush. Jess was right. The attention is so intoxicating. But I only wanted Connor for now. I still needed to hear him say those words again. I needed to feel his cock inside of me again, hopefully in my boi pussy instead of just my mouth.

The party went on for a while. It all seems like a blur at this point. I was so drunk off of the alcohol and the rush of being dressed as a sexy girl in front of all of my friends. I heard Connor whisper in my ear that he wanted to go upstairs to make another drink. He grabbed my hand, so I followed him, passing Jess on the way. She winked at me as she continued dancing with another one of my other pledge brothers.

We got to the room and Connor quickly locked the door behind us.

"Alright, bitch. I can't wait anymore. I have a weeks worth of cum that I need to give you. Get on your knees."

He slid his robe off as I dropped to my knees in front of him, eager to see his cock again. I slipped his boxers off and felt his hard cock hit me in the face as I did. Gosh, he was so big.

I put my hands behind my back like I knew he liked and started bobbing on his dick. I felt both of his hands on the back of my head as he started to face fuck me. I only blew him for a minute or so before he pulled out of my mouth. He slapped the side of my face with his cock a few times as I looked up into his eyes desperately. My caged clit was leaking so much.